EP0380312A1 - Composés pesticides - Google Patents

Composés pesticides Download PDF

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Publication number
EP0380312A1
EP0380312A1 EP90300721A EP90300721A EP0380312A1 EP 0380312 A1 EP0380312 A1 EP 0380312A1 EP 90300721 A EP90300721 A EP 90300721A EP 90300721 A EP90300721 A EP 90300721A EP 0380312 A1 EP0380312 A1 EP 0380312A1
Authority
EP
European Patent Office
Prior art keywords
group
compound
optionally substituted
fluoro
halo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP90300721A
Other languages
German (de)
English (en)
Inventor
John Patrick Larkin
John Bernard Weston
Ian Harold Smith
Christopher John Palmer
John Edward Casida
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
University of California
Original Assignee
Roussel Uclaf SA
Wellcome Foundation Ltd
University of California
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB8901490A external-priority patent/GB8901490D0/en
Priority claimed from GB898901491A external-priority patent/GB8901491D0/en
Application filed by Roussel Uclaf SA, Wellcome Foundation Ltd, University of California filed Critical Roussel Uclaf SA
Publication of EP0380312A1 publication Critical patent/EP0380312A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D497/08—Bridged systems

Definitions

  • the present invention relates to novel chemical compounds having pesticidal activity, to methods for their preparation, to compositions containing them and to their use in the control of pests. More particularly the invention relates to a class of heterobicycloalkanes.
  • the present invention provides a compound of the formula (I): wherein R is a phenyl group, substituted by 1 to 5 fluorine atoms and optionally substituted at the para position by methyl or chloro or R is a group being a three or four membered ring, where R4 is oxygen or a group CR7R8 wherein groups R7, R8 are the same or different and each is hydrogen, fluoro, chloro or bromo or methyl or ethyl optionally substituted by 1 to 3 fluoro atoms, and when is a three-membered ring R5 is a group CR 7a R 8a wherein R 7a , R 8a are the same or different and each is hydrogen, fluoro, chloro or bromo or methyl or ethyl optionally substituted by 1 to 3 fluoro atoms, or when is a four membered ring R5 is a group CR 7a R 8a CR9R10 wherein R 7a ,
  • halo is meant fluoro, chloro, bromo or iodo.
  • non-aromatic hydrocarbyl an alkyl, alkenyl or alkynyl group (including a cyclic alkyl or alkenyl group optionally substituted by alkyl, alkenyl or alkynyl; and alkyl or alkenyl substituted by cyclic alkyl and alkenyl).
  • 6-membered aromatic ring is meant phenyl and heteroaromatic rings such as pyridyl.
  • R is a phenyl group substituted by 1 to 5 fluorine atoms and optionally substituted at the para position by methyl or chloro.
  • R is phenyl substituted by one or two fluorine atoms.
  • R is a group as hereinbefore defined.
  • R is a cyclopropyl or cyclobutyl group, each optionally substituted by methyl.
  • R1 is hydrogen, cyano, methyl or ethyl each optionally substituted by cyano, methoxy, methylthio, chloro, bromo or fluoro. Most suitably R1 is hydrogen, methyl, cyano or trifluoromethyl. Preferably R1 is hydrogen.
  • R2 is hydrogen, cyano, methyl or trifluoromethyl.
  • R2 is hydrogen.
  • R3 suitably contains between 3 and 12 carbon atoms. Preferably there is only one silyl group present. The sulphur atoms present may be in an oxidised form if desired. Preferably there is a maximum of two sulphur atoms present in R3. Suitably there is a maximum of four and preferably a maximum of three oxygen atoms in R3. Preferably there is only one nitrogen atom present in R3.
  • R3 is suitably a C3 ⁇ 9 alkyl, alkenyl or alkynyl group, each of which may be optionally substituted by halo or a group R13, or R3 is a substituted phenyl or cyclohexyl group.
  • the group R13 is linked to the hydrocarbyl group via a hetero atom of R13.
  • Suitable substituents R13 for the group R12 include alkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, acyloxy, alkynyloximino, trialkylsilyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkyloximino, alkoxycarbonyloxy and mono or di-substituted alkylamino groups or a group -(O) n S(O) r (O) w R19 wherein R19 is a C1 ⁇ 4 aliphatic group optionally substituted by halo, n is 0 or 1, r is 0, 1 or 2 and w is 0 or 1, the sum of n, r and w being between 0 and 3.
  • substituents R13 include alkoxy, alkoxyalkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy and haloalkynyloxy.
  • R12 is substituted by up to two substituents R13 and preferably R12 is unsubstituted or contains one substituent R13.
  • R3 is a phenyl group substituted at the 3-,4- or 5-positions by one to three substituents each selected from halo, C1 ⁇ 4 haloalkyl, cyano, or a group (C ⁇ C) p R20 wherein p is 1 or 2 and R20 is hydrogen, bromo, chloro, iodo; or R20 is an aliphatic group containing up to five carbon atoms optionally substituted by C1 ⁇ 4 alkoxy, C1 ⁇ 6 alkoxyalkoxy, C1 ⁇ 8 acyloxy, halo or hydroxy; or R20 is SiR16 R17 R18 wherein R16 R17 and R18 are as hereinbefore defined.
  • R3 is a substituted phenyl group it is additionally optionally substituted at the 2- and/or 6-positions by fluoro or chloro.
  • R3 is phenyl substituted at the 3-, 4- or 5- positions by one to three substituents each selected from halo, cyano, C1 ⁇ 4 haloalkyl or a group C ⁇ C-R21 where R21 is hydrogen, or methyl or ethyl each optionally substituted by hydroxy, methoxy, ethoxy, acetoxy; or R21 is ethynyl, or a silyl group substituted by three C1 ⁇ 4 alkyl groups, R3 is additionally optionally substituted at the 2- and/or 6- positions by fluoro or chloro.
  • R3 is phenyl para substituted by a group -C ⁇ C-R22 wherein R22 is hydrogen.
  • R3 is a group -B(C ⁇ C)Z, wherein B is a C3 ⁇ 5 aliphatic chain optionally containing a double bond and/or an oxygen atom and/or a group S(O) q wherein q is 0, 1 or 2, and optionally substituted by halo, C1 ⁇ 4 alkyl, C1 ⁇ 4 haloalkyl, C2 ⁇ 4 carbalkoxy or cyano and Z is hydrogen, C1 ⁇ 5 alkyl, C1 ⁇ 3 alkoxymethyl or a group SiR16 R17 R18 wherein R16, R17 and R18 are as hereinbefore defined.
  • R3 is a group -DZ1, wherein D is a group -CH2O- or CH2S(O) q wherein q is 0, 1 or 2 or a C2 ⁇ 3 aliphatic group each of which may be optionally substituted by one to three halo atoms and Z1 is silyl substituted by three C1 ⁇ 4 alkyl groups or Z1 is a group wherein R23, R24 and R25 are the same or different and are each independently selected from halo, cyano, C2 ⁇ 5 carbalkoxy, or a C1 ⁇ 4 aliphatic group optionally substituted by halo,cyano, C2 ⁇ 5 carbalkoxy, C1 ⁇ 4 alkoxy or a group S(O) q R26 wherein q is 0, 1 or 2 and R26 is C1 ⁇ 4 alkyl, or R23, R24 and R25 are selected from C1 ⁇ 4 alkoxy or a group S(O) z R27 wherein z is 0, 1 or
  • R4 is oxygen, CH2, CF2 CHMe or C(Me)2.
  • R5 is CH2, CF2, C(Me)2 or CH2CH2.
  • R6 is hydrogen or methyl.
  • aliphatic group is meant an alkyl, alkenyl or alkynyl group.
  • Z1 is tertiary butyl, trichloromethyl or 2-methoxyprop-­2-yl.
  • R3 is a group wherein Z is as hereinbefore defined:
  • a preferred group of compounds of the formula (I) is that in which R3 contains a -(C ⁇ C)- fragment or terminates in a group Z1 as hereinbefore defined.
  • the compounds of the formula (I) may exist in a number of isomeric forms.
  • the present invention provides individual isomers of compounds of the formula (I) and mixtures thereof.
  • the present invention also encompasses compounds of the formula (I) containing radioisotopes, particularly those in which one carbon atoms is C14 or one to three hydrogen atoms are replaced by tritium.
  • the present invention provides a process for the preparation of a compound of the formula (I).
  • the process for the preparation of a compound of the formula (I) may be any method known in the art for preparing analogous compounds, for example :
  • the compounds of the formula (II) may be prepared by the reaction of compounds of the formulae (III) and (IV): where R to R3 are as hereinbefore defined and L is a leaving group such as halo or hydroxy.
  • This reaction conveniently takes place under conditions well known to those skilled in the art, for example when L is halo in an inert solvent in the presence of base at a non-extreme temperature and when L is hydroxy in an inert solvent in the presence of a condensing agent at a non extreme temperature.
  • halogenated hydrocarbons such as dichloromethane
  • pyridine is a preferred base
  • L hydroxy
  • dimethylformamide is a suitable solvent
  • dicyclohexylcarbodi­imide is a preferred condensing agent
  • the reaction will conveniently be carried out at between -50 and 100 o C, preferably between 0 and 25 o C.
  • the compounds of the formula III may be prepared as described in copending European Patent Applications Nos. 211598 and 216624.
  • the compounds of the formula (IV) may be prepared by methods well known to those skilled in the art.
  • the reaction can also be carried out in methanol containing hydrogen chloride.
  • the reaction is conveniently carried out at a non-extreme temperature, for example between -70 o C and 150 o C and normally between -10 o C and 150 o C.
  • the compounds of the formula (V) may be prepared as described in European Patent Application No 216624.
  • the compounds of the formula (AlkO)3C R3 may be prepared by a general procedure for the synthesis of orthoesters and is described by S.M.McElvain and R.E.Starn, J.Amer.Chem.Soc ., 1955, 77 , 4571:
  • Novel chemical intermediates also form an important aspect of the present invention.
  • Preferred intermediates include those of the formula (II), (V), (VII), (XIV) and (XV).
  • the compounds of formula (I) may be used to control pests such as arthropods e.g. insect and acarine pests, and helminths, i.e. nematodes.
  • arthropods e.g. insect and acarine pests
  • helminths i.e. nematodes.
  • the present invention provides a method for the control of arthropods and/or helminths which comprises administering to the arthropod and/or helminth or to their environment an arthropodically effective amount of a compound of the formula (I).
  • the present invention also provides a method for the control and/or eradication of arthropod and/or helminth infestations of animals (including humans) and/or of plants,(including trees) and/or stored products which comprises administering to the animal or locus an effective amount of a compound of the formula (I).
  • the present invention further provides for the compounds of the formula (I) for use in human and veterinary medicine, in public health control and in agriculture for the control of arthropod and/or helminth pests.
  • the compounds of formula (I) are of particular value in the protection of field, forage, plantation, glasshouse, orchard and vineyard crops, of ornamentals and of plantation and forest trees, for example, cereals (such as maize, wheat, rice, sorghum), cotton, tobacco, vegetables and salads (such as beans, cole crops, curcurbits, lettuce, onions, tomatoes and peppers), field crops (such as potato, sugar beet, ground nuts, soyabean, oil seed rape), sugar cane, grassland and forage (such as maize, sorghum, lucerne), plantations (such as of tea, coffee, cocoa, banana, oil palm, coconut, rubber, spices), orchards and groves (such as of stone and pip fruit, citrus, kiwifruit, avocado, mango, olives and walnuts), vineyards, ornamental plants, flowers and shrubs under glass and in gardens and parks, forest trees (both deciduous and evergreen) in forests, plantations and nurseries.
  • cereals such as maize
  • the compounds of general formula I are of particular value in the control of arthropods or helminths which are injurious to, or spread or act as vectors of diseases in man and domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges and biting, nuisance and myiasis flies.
  • the compounds of Formula (I) may be used for such purposes by application of the compounds themselves or in diluted form in known fashion as a dip, spray, fog, lacquer, foam, dust, powder, aqueous suspension, paste, gel, cream, shampoo, grease, combustible solid, vapourising mat, combustible soil, bait, dietary supplement, wettable powder, granule, aerosol, emulsifiable concentrate, oil suspensions, oil solutions, pressure-pack, impregnated article, pour on formulation or other standard formulations well known to those skilled in the art. Dip concentrates are not applied per se , but diluted with water and the animals immersed in a dipping bath containing the dip wash.
  • Sprays may be applied by hand or by means of a spray race or arch.
  • the animal, soil, plant or surface being treated may be saturated with the spray by means of high volume application or superficially coated with the spray by means of light or ultra low volume application.
  • Aqueous suspensions may be applied in the same manner as sprays or dips.
  • Dusts may be distributed by means of a powder applicator or, in the case of animals, incorporated in perforated bags attached to trees or rubbing bars.
  • Pastes, shampoos and greases may be applied manually or distributed over the surface of an inert material, such as that against which animals rub and transfer the material to their skins.
  • Pour-on formulations are dispensed as a unit of liquid of small volume on to the backs of animals such that all or most of the liquid is retained on the animals.
  • the compounds of Formula (I) may be prepared either as formulations ready for use on the animals, plants or surface or as formulations requiring dilution prior to application, but both types of formulation comprise a compound of Formula (I) in intimate admixture with one or more carriers or diluents.
  • the carriers may be liquid, solid or gaseous or comprise mixtures of such substances, and the compound of Formula (I) may be present in a concentration of from 0.025 to 99% w/v depending upon whether the formulation requires further dilution.
  • Dusts, powders and granules and other solid formulations comprise the compound of Formula (I) in intimate admixture with a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, adsorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carriers, starch and diatomaceus earths.
  • a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, adsorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carriers, starch and diatomaceus earths.
  • Such solid formulations are generally prepared by impregnating the solid diluents with solutions of the compound of formula (I) in volatile solvents, evaporating the solvents and, if desired grinding the products so as to
  • Sprays of a compound of Formula (I) may comprise a solution in an organic solvent (e.g. those listed below) or an emulsion in water (dip wash or spray wash) prepared in the field from an emulsifiable concentrate (otherwise known as a water miscible oil) which may also be used for dipping purposes.
  • the concentrate preferably comprises a mixture of the active ingredient, with or without an organic solvent and one or more emulsifiers.
  • Solvents may be present within wide limits but preferably in an amount of from 0 to 90% w/v of the composition and may be selected from kerosene, ketones, alcohols, xylene, aromatic naphtha, and other solvents known in the formulating art.
  • the concentration of emulsifiers may be varied within wide limits but is preferably in the range of 5 to 25% w/v and the emulsifiers are conveniently non-ionic surface active agents including polyoxyalkylene esters of alkyl phenols and polyoxyethylene derivatives of hexitol anhydrides and anionic surface active agents including Na lauryl sulphate, fatty alcohol ether sulphates, Na and Ca salts of alkyl aryl sulphonates and alkyl sulphosuccinates.
  • Cationic emulsifiers include benzalkonium chloride and quaternary ammonium ethosuphates.
  • Amphoteric emulsifiers include carboxymethylated oleic imidazoline and alkyl dimethyl betain.
  • Vaporising mats normally comprise cotton and cellulose mix compressed into a board of approximately 35 x 22 x 3mm dimensions, treated with up to 0.3ml of concentrate comprising the active ingredient in an organic solvent and optionally an antioxidant, dye and perfume.
  • the insecticide is vaporised using a heat source such as an electrically operated mat heater.
  • Combustible solids normally comprise of wood powder and binder mixed with the active ingredient and formed into shaped (usually coiled) strips. Dye and fungicide may also be added. Wettable powders comprise an inert solid carrier, one or more surface active agents, and optionally stabilisers and/or anti-oxidants.
  • Emulsifiable concentrates comprise emulsifying agents, and often an organic solvent, such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
  • organic solvent such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
  • Wettable powders and emulsifiable concentrates will normally contain from 5 to 95% by weight of the active ingredient, and are diluted, for example with water, before use.
  • Lacquers comprise a solution of the active ingredient in an organic solvent, together with a resin, and optionally a plasticiser.
  • Dip washes may be prepared not only from emulsifiable concentrates but also from wettable powders, soap based dips and aqueous suspensions comprising a compound of Formula (I) in intimate admixture with a dispersing agent and one or more surface active agents.
  • Aqueous suspensions of a compound of Formula (I) may comprise a suspension in water together with suspending, stabilizing or other agents.
  • the suspensions or solutions may be applied per se or in a diluted form in known fashion.
  • Greases may be prepared from vegetable oils, synthetic esters of fatty acids or wool fat together with an inert base such as soft paraffin. A compound of Formula (I) is preferably distributed uniformly through the mixture in solution or suspension. Greases may also be made from emulsifiable concentrates by diluting them with an ointment base.
  • Pastes and shampoos are also semi-solid preparations in which a compound of Formula (I) may be present as an uniform dispersion in a suitable base such as soft or liquid paraffin or made on a non-greasy basis with glycerin, mucilage or a suitable soap.
  • a suitable base such as soft or liquid paraffin or made on a non-greasy basis with glycerin, mucilage or a suitable soap.
  • shampoos and pastes are usually applied without further dilution they should contain the appropriate percentage of the compound of Formula (I) required for treatment.
  • Aerosol sprays may be prepared as a simple solution of the active ingredient in the aerosol propellant and co-solvent such as halogenated alkanes and the solvents referred to above, respectively.
  • Pour-on formulations may be made as a solution or suspension of a compound of Formula (I) in a liquid medium.
  • An avian or mammal host may also be protected against infestation of acarine ectoparasites by means of carrying a suitably-moulded, shaped plastics article impregnated with a compound of Formula (I).
  • Such articles include impregnated collars, tags, bands, sheets and strips suitably attached to appropriate parts of the body.
  • the plastics material is a polyvinyl chloride (PVC).
  • the concentration of the compound of Formula (I) to be applied to an animal, premises or outdoor areas will vary according to the compound chosen, the interval between treatments, the nature of the formulation and the likely infestation, but in general 0.001 to 20.0% w/v and preferably 0.01 to 10% of the compound should be present in the applied formulation.
  • the amount of the compound deposited on an animal will vary according to the method of application, size of the animal, concentration of the compound in the applied formulation, factor by which the formulation is diluted and the nature of the formulation but in general will lie in the range of from 0.0001% to 0.5% w/w except for undiluted formulations such as pour-on formulations which in general will be deposited at a concentration in the range from 0.1 to 20.0% and preferably 0.1 to 10%.
  • the amount of compound to be applied to stored products in general will lie in the range of from 0.1 to 20ppm. Space sprays may be applied to give an average initial concentration of 0.001 to 1mg of compound of formula (I) per cubic metre of treated space.
  • the compounds of formula (I) are also of use in the protection and treatment of plant species, in which case an effective insecticidal, acaricidal or nematocidal amount of the active ingredient is applied.
  • the application rate will vary according to the compound chosen, the nature of the formulation, the mode of application, the plant species, the planting density and likely infestation and other like factors but in general, a suitable use rate for agricultural crops is in the range 0.001 to 3kg/Ha and preferably between 0.01 and 1kg/Ha.
  • Typical formulations for agricultural use contain between 0.0001% and 50% of a compound of formula (I) and conveniently between 0.1 and 15% by weight of a compound of the formula (I).
  • Dusts, greases, pastes and aerosol formulations are usually applied in a random fashion as described above and concentrations of 0.001 to 20% w/v of a compound of Formula (I) in the applied formulation may be used.
  • the compounds of formula (I) have been found to have activity against the common housefly (Musca domestica) .
  • certain compounds of formula (I) have activity against other arthropod pests including Myzus persicae, Tetranychus urticae, Plutella xylostella , Culex spp. Tribolium castaneum , Sitophilus granarius , Periplaneta amiercana and Blattella germanica .
  • the compounds of formula (I) are thus useful in the control of arthropods e.g. insects and acarines in any environment where these constitute pests, e.g. in agriculture, in aminal husbandry, in public health control and in domestic situations.
  • Insect pests include members of the orders Coleoptera (e.g. Anobium , Ceutorhynchus,Rhynchophorus, Cosmopolites , Lissorhoptrus, Meligethes , Hypothenemus , Hylesinus , Acalymma , Lema , Psylliodes , Leptinotarsa , Gonocephalum , Agriotes , Dermolepida , Heteronychus , Phaedon , Tribolium , Sitophilus , Diabrotica , Anthonomus or Anthrenus spp.), Lepidoptera (e.g. Anobium , Ceutorhynchus,Rhynchophorus, Cosmopolites , Lissorhoptrus, Meligethes , Hypothenemus , Hylesinus , Acalymma , Lema , Psylliodes , Leptinotarsa
  • Ephestia Mamestra , Earias , Pectinophora , Ostrinia , Trichoplusia , Pieris , Laphygma, Agrotis , Amathes , Wiseana , Tryporysa , Diatraea , Sporganothis , Cydia , Archips , Plutella , Chilo , Heliothis , Spodoptera or Tineola spp.), Diptera (e.g.
  • Musca Aedes , Anopheles , Culex , Glossina , Simulium , Stomoxys , Haematobia , Tabanus , Hydrotaea , Lucilia , Chrysomia , Callitroga , Dermatobia , Gasterophilus , Hypoderma , Hylemyia , Atherigona , Chlorops, Phytomyza , Ceratitis , Liriomyza and Melophagus spp.), Phthiraptera ( Malophaga e.g. Damalina spp. and Anoplura e.g.
  • Hemiptera e.g. Aphis , Bemisia , Phorodon , Aeneolamia , Empoasca , Parkinsiella , Pyrilla , Aonidiella , Coccus , Pseudococus, Helopeltis , Lygus , Dysdercus , Oxycarenus , Nezara , Aleurodes , Triatoma , Psylla , Myzus , Megoura , Phylloxera , Adelyes , Niloparvata , Nephrotetix or Cimex spp.), Orthoptera (e.g. Aphis , Bemisia , Phorodon , Aeneolamia , Empoasca , Parkinsiella , Pyrilla , Aonidiella , Coccus , Pseudococus, Helopeltis , Lygus , Dy
  • Locusta Locusta , Gryllus , Schistocerca or Acheta spp.
  • Dictyoptera e.g. Blattella , Periplaneta or Blatta spp.
  • Hymenoptera e.g. Athalia , Cephus , Atta , Solenopsis or Monomorium spp.
  • Isoptera e.g. Odontotermes and Recticulitermes spp.
  • Siphonaptera e.g. Ctenocephalides or Pulex spp.
  • Thysanura e.g. Lepisma spp.
  • Dermaptera e.g. Forficula spp.
  • Pscoptera e.g. Peripsocus spp.
  • Thysanoptera e.g. Thrips tabaci
  • Acarine pests include ticks, e.g. members of the genera Boophilus , Ornithodorus , Rhipicephalus , Amblyomma , Hyalomma , Ixodes , Haemaphysalis , Dermacentor and Anocentor , and mites and manges such as Acarus , Tetranychus , Psoroptes , Notoednes , Sarcoptes , Psorergates , Chorioptes, Eutrombicula , Demodex, Panonychus , Bryobia , Eriophyes , Blaniulus , Polyphagotarsonemus , Scutigerella , and Oniscus spp.
  • ticks e.g. members of the genera Boophilus , Ornithodorus , Rhipicephalus , Amblyomma , Hyalomma , Ixodes , Haemaphysalis
  • Nematodes which attack plants and trees of importance to agriculture, forestry, horticulture either directly or by spreading bacterial, viral, mycoplasma or, fungal diseases of the plants include root-knot nematodes such as Meloidogyne spp. (e.g. M . incognita ); cyst nematodes such as Globodera spp. (e.g. G . rostochiensis ); Heterodera spp. (e.g. H . avenae); Radopholus spp. (e.g. R . similis ); lesion nematodes such as Pratylenchus spp. (e.g. P .
  • root-knot nematodes such as Meloidogyne spp. (e.g. M . incognita ); cyst nematodes such as Globodera spp. (e.g. G . rostochiensis );
  • Belonolaimus spp. e.g. B . gracilis
  • Tylenchulus spp. e.g. T . semipenetrans
  • Rotylenchulus spp. e.g. R . reniformis
  • Rotylenchus spp. e.g. R . robustus
  • Helicotylenchus spp. e.g. H . multicinctus
  • Hemicycliophora spp. e.g. H . gracilis
  • Criconemoides spp. e.g. C . similis
  • Trichodorus spp. e.g.
  • T primitivus dagger nematodes such as Xiphinema spp. (e.g. X . diversicaudatum ), Longidorus spp (e.g. L . elongatus ); Hoplolaimus spp. (e.g. H . coronatus ); Aphelenchoides spp. (e.g. A . ritzema-bosi , A . besseyi); stem and bulb eelworms such as Ditylenchus spp. (e.g. D . dipsaci .
  • dagger nematodes such as Xiphinema spp. (e.g. X . diversicaudatum ), Longidorus spp (e.g. L . elongatus ); Hoplolaimus spp. (e.g. H . coronatus ); Aphelenchoides spp.
  • Compounds of the invention may be combined with one or more other pesticidally active ingredients (for example pyrethroids, carbamates and organophosphates) and/or with attractants, repellents, bacteriocides, fungicides, nematocides, anthelmintics and the like. Furthermore, it has been found that the activity of the compounds of the invention may be enhanced by the addition of a synergist or potentiator, for example: one of the oxidase inhibitor class of synergists, such as piperonyl butoxide or propyl 2-propynylphenylphosphonate; a second compound of the invention; or a pyrethroid pesticidal compound.
  • a synergist or potentiator for example: one of the oxidase inhibitor class of synergists, such as piperonyl butoxide or propyl 2-propynylphenylphosphonate; a second compound of the invention; or a pyr
  • Stabilisers for preventing any chemical degradation which may occur with the compounds of the invention include, for example, antioxidants (such as tocopherols, butylhydroxyanisole and butylhydroxytoluene) and scavengers (such as epichlorhydrin) and organic or inorganic bases e.g. trialkylamines such as triethylamine which can act as basic stabilises and as scavengers.
  • antioxidants such as tocopherols, butylhydroxyanisole and butylhydroxytoluene
  • scavengers such as epichlorhydrin
  • organic or inorganic bases e.g. trialkylamines such as triethylamine which can act as basic stabilises and as scavengers.
  • Microemulsion Compound of formula (I) 10.00 Polyoxyethylene glycerol monooleate* 10.00 Alkane diol 4.00 Water 76.00 100.00 * Surfactant 9.
  • Water Dispersible Granules Compound of formula (I) 70.00 Polyvinyl pyrrolidine 2.50 Alkyl aryl ethoxylate 1.25 Alkyl aryl sulphonate 1.25 China clay 25.00 100.00 10.
  • cyclopropyl malonate ester starting materials were prepared as follows:- Cyclopropanecarbonyl chloride (36g, 0.34mol) was added dropwise to a stirred solution of ethyl diazoacetate (86.2g, 0.76mol) in dry ether (500ml) at 0°C under a nitrogen atmosphere. The mixture was allowed to warm to room temperature then was stirred for 1 day, heated to gentle reflux for 2 days, then left to stand at room temperature for 5 days. Evaporation of the mixture followed by distillation afforded ethyl 3-cyclopropyl-2-diazo-­3-oxo-propanoate (27.4g, 44%) bp 85-90° at 1mm Hg).
  • the compounds of the invention were tested by dissolving the compounds in acetone (5%) and then diluting in water: 'Symperonic' (94.5%: 0.5%) to give a water emulsion. The solution was then used to treat the following insects.
  • Leaf discs of infested french bean were sprayed with the solution containing the compound. Mortality was assessed after 2 days at 25°C.
  • a chinese cabbage leaf was sprayed with the solution of the compound and left to dry. It was infested with 10 newly hatched Spodoptera larvae. Mortality was assassed after 3 days at 25°C.
  • Filter paper and food were sprayed and subsequently infested with 10 second instar larvae. Mortality was assessed after 48 hours.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
EP90300721A 1989-01-24 1990-01-23 Composés pesticides Withdrawn EP0380312A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8901490A GB8901490D0 (en) 1989-01-24 1989-01-24 Pesticidal compounds
GB8901490 1989-01-24
GB898901491A GB8901491D0 (en) 1989-01-24 1989-01-24 Pesticidal compounds
GB8901491 1989-01-24

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EP0380312A1 true EP0380312A1 (fr) 1990-08-01

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EP (1) EP0380312A1 (fr)
JP (1) JPH02262582A (fr)
CA (1) CA2008348A1 (fr)
DK (1) DK0380312T3 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5905176A (en) * 1998-08-28 1999-05-18 Eastman Chemical Company Process for the production of cyclobutyl halides
US6077981A (en) * 1998-08-28 2000-06-20 Eastman Chemical Company Process for the production of cyclopropylmethyl halides
US6090982A (en) * 1999-08-03 2000-07-18 Eastman Chemical Company Process for the preparation of cyclopropylglycine
US6207854B1 (en) 1999-12-15 2001-03-27 Eastman Chemical Company Preparation of 3-amino-3-cyclopropylpropanoate esters

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5729149B2 (ja) * 2011-06-08 2015-06-03 Jnc株式会社 液晶組成物および液晶表示素子

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0243184A2 (fr) * 1986-04-25 1987-10-28 Roussel-Uclaf Composés pesticides
EP0279698A2 (fr) * 1987-02-20 1988-08-24 The Wellcome Foundation Limited Composés pesticides
US4772624A (en) * 1985-01-23 1988-09-20 The Regents Of The University Of California 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)-octanes having ethynyl substituted phenyl group

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4772624A (en) * 1985-01-23 1988-09-20 The Regents Of The University Of California 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)-octanes having ethynyl substituted phenyl group
EP0243184A2 (fr) * 1986-04-25 1987-10-28 Roussel-Uclaf Composés pesticides
EP0279698A2 (fr) * 1987-02-20 1988-08-24 The Wellcome Foundation Limited Composés pesticides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5905176A (en) * 1998-08-28 1999-05-18 Eastman Chemical Company Process for the production of cyclobutyl halides
US6077981A (en) * 1998-08-28 2000-06-20 Eastman Chemical Company Process for the production of cyclopropylmethyl halides
US6090982A (en) * 1999-08-03 2000-07-18 Eastman Chemical Company Process for the preparation of cyclopropylglycine
US6103929A (en) * 1999-08-03 2000-08-15 Eastman Chemical Company Process for the preparation of cyclopropylglycine
US6207854B1 (en) 1999-12-15 2001-03-27 Eastman Chemical Company Preparation of 3-amino-3-cyclopropylpropanoate esters

Also Published As

Publication number Publication date
DK0380312T3 (da) 1990-08-01
JPH02262582A (ja) 1990-10-25
CA2008348A1 (fr) 1990-07-24

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